Jasoslav prohlich



Patented Mar. 9, i926.

UNITED STATES PATENT OFFICE.

JAIlOSLAV FRbI-ILICH, OF BASEL, SWITZERLAND, ASSIG-NOR TO SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SVVITZERLANDf DYESTUFFS AND PROCESS OF MAKING SAME.

No Drawing.

T 0 all whom it may concern:

Be it known that I, JAROSLAV Fnorrmon, a citizen of the Swiss Confederation, and residing at Basel, Switzerland, have invented useful new Dyestuffs and Processes of Making Same, of which the following is a full, clear, and exact specification.

The present invention relates to new vat dyestuffs which are particularly valuable for producing fast tints on the-- animal fibre. The invention comprises the new dyestuffs,

- the method of making same, and the material dyed with the new vatdyestuifs.

It has been found that valuable vat deystuffs are obtained by causing sulfur monochloride S Cl to act upon 2:5-diarylidobenzoquinones at temperatures that do not exceed 100 C. This reaction may be conducted in presence of a diluent and with addition of an agent which binds acids, as for example sodium acetate or magnesium oxide, and a condensing agent, as for example sulphuric acid. The proportions which the reacting substances bearto each other may be varied within wide limits.

Particularly suitable for the-reaction are 2:5-diarylidobenzoquinones, which are not substituted or are only 111ono substituted (in 8- or (S-position) in the quinone nucleus. The 2:5-diarylidobenzoquinones, the manufacture of whichis generally known, may be derived from two aromatic amines which may be the same or different and may be mono-substituted. at the nitrogen or monoor poly-substituted in any position of the nucleus. As substituents there nay be named, among others, halogen, alkyl-, alk oxyl- (QCIL), phenyloxy- (00 11 nitro-, amino-, alkylamino-, aralkylamind, phenylamino-, hydroxyl or carboxyl-groups he dyestuffs thus obtained form dark, yellow to dark blue and black powders and contain sulphur and mostly also halogen. They dissolve in concentrated sulphuric acid to a-brown to red-violet and blue green solution. With hydrosulphite and caustic soda lye they give bright yellow to brown vats from which wool is dyed fast yellowbrown to red-brown, olive-green, green and grey tints.

The following examples illustrate their}:

Application filed Novembcr 7, 1924:. Serial No. 748,492.

vention Without,however, limiting the scope of the same, the partsbeing by weight Example 1.

7.2 parts of 2:5-dianilidobenzoquinone' corresponding with the formula:

are suspended in 14% parts of nitrobenzene and 11 parts of sulphur monochloride (S Cl are added at 2-6" C. while stirring well. After continued stirring the mixture is filtered, and the solid product washed and dried. It is a brown powder which dissolves in concentrated sulphuric acid to a dirty blue solution and dyes wool in a hydrosulphite vat fast brownish tints.

In a similar manner brown-dyeing dyestuffs containing sulphur and halogen and dissolving in sulphuric acid with violet to blue color are obtained from'2 :5-di (B-naphthylamido)-benzoquinone and from 2:5-

-diparatoluididobenzoquinone.

Dyestuffs giving yellow or, respectively, greenish-grey tints are obtained from 2:5- diparaoxyanilidobenzoquinone or, respectively, from 2:5-dimetaanilidobenzoquinone.

If the reaction of 2:5-dianilidobenzoquinone on sulphur chloride is conducted in the presence of an agent adapted to bind acid, such as magnesia. there is obtained a dyestuif of like properties which dyes wool in the vat dark brown tints, while addition of sodium acetate shifts the tint towards olive.

Emamplc 2 solid matter being washed and dried. The 4.. As a new process, the manufacture of dyestuff formed is a greenish-black powder, soluble in concentrated sulphuric acid to a dirty violet solution. With hydrosulphite and causticsoda lye it ives a bright yellow ish "at which dyes wool fast green tints.

It the reaction be interrupted at an earlier there is produced a (lyeitii fl with a" yellow-green tint.

Emample 3.

40 parts of 2 5-dianilido-0-chloro-1 it-benzoquinone are suspended in 800 parts of nitrobenzene' and the suspensi'oi'i is mixed at 5 C. with 50.5 parts'of"sulphur monochloride and thewhole is thoroughly stirred for a long time at this temperature. It is then diluted with alcohol, filtered "andth'e solid matter washeli and" dried." "1h'e"nc-w (ii e stuff forms a brownislpyellow powder which dissolves in concentrated sulphuric acid. to a violet solution and dyes wool fast yellowbrown tints in the vat.

The substitution of 2 5dian ilido-(Mnethyl- 1 :l-benzoquinone for the 2:5-diani'lido-(3- chlOlo-l -l-benzoquinone produces a. dye-stun which is a. red-violet powdersoluble in sulphuric acid to' a dull gi'ee'nish lilue so lutioii' and dyeing wool in 'the vat blackish-brown.

1. As a newproc'ess, the m'mmfaeuueof vat dyeitulfs, which consists'in c agingss1- phur inonochlori de "to act upon 2 -diaiylidobenzoquinones at 'teiiiperatuies not exceeding 1.00 O.

2. As a new process, the nmmnicuue of at dyestiiiflis, which consists in' ca'using sulphur inonoe-liloride to actuponQ-f 5-diai'ylidobenzoquinones in' presence ofa. diluent attemperatures not exceeding} 100 (l.

As anew processfthe manufacture of vat dyestuffs, which consists inca'usinn sulphur inonochloride to act 111 011 2; fi-di'anilidobcnzoquinone at teiiipei'atuies not eftce'eding 100 C.

vat dyestuffs, which consists in causing sulphur inonochloride to act upon 2: fi-dianilidobenzoquinone in presence of a diluent at tei'nperatnres not exceeding 100 C.

As new products, the dyestuffs obtained as described from 2: 5-diarylidobenzoquinones and sulphur inon'ochlori'd'e; which form dark yellow'to' dark blue and black powders, dissolvingin concentrated sulphuric acid to brown'to red-violet and blue-green solutions andgiving with hydrosulphite and caustic soda lye bright yellow to brown vats from which wool is dyed fast yello\\'-bro\\u1 to red brown, olive-green, green and grey tints.

6i As-new' products,,the dyestuffs obtained as described from 2:5-diarylidobenzoquinones and sulphur njionochloride containing sulphur and.alsofchlorineywhich form dark yellow to dark blue-and black powders, -dissolving in concentrated sulphuric acid to brownto red-violet'and blue-"green solutions andpgivingwith hydrosulphite and caustic soda; lye bright yellow to hrownflatv from which wo'olis dyed fast'yellow brown'iored brown, olive-green;greenand grey tints.

'7. As new productsithe dyestulis obtained as described from 2': 5-dianilidobenzoiuii- 1101163 and sulphur inonochloride containing sulphur and also chlorine, which form dark yellow to dark blue andblack powders, (lissolving in concentrated sulphuric acid to violet to blue solutions and giving wi'tl hydrosulphite and caustic soda lye bright yellow to brown vats t'ro'm which wool is dyed fast brown to green tints.

S. lilaterial dyed with the claim 9. Material dyed. with claim 6.

10. Material dyed with'the dyestuffs of claim 7.

In witness whereof I have hereunto gned my naine'this 24th: day of October 1921.

JAROSLAV FRornJoi-i.

dyestuffs o' 

